Expeditious and highly efficient synthesis of propargylamines using a Pd‐Cu nanowires catalyst under solvent‐free conditions

Abstract

A heterogeneous Pd-Cu NWs-catalyzed expeditious and solvent-free synthesis of propargylamines via A 3 -coupling of aldehydes, alkynes, and amines has been proposed. A wide range of aldehydes, alkynes and amine substrates undergo A 3 -coupling to produce propargylamines in good to excellent yields with good functional tolerance, such as that towards alkoxy, hydroxy, C-X (X = F, Cl, Br) as well as amide and C=C bonds. Furthermore, the catalyst could be recovered easily and reused for at least 5 cycles without showing significant loss of catalytic activity.

Applications of bimetallic PdCu catalysts

“…The three-component coupling of an aldehyde, an amine and an acetylene, named A 3 -coupling, is a direct method for the synthesis of propargylamines. 57 Liang, Xu and coworkers 58 have recently used PdCu-NWs 22 for the A 3 -coupling of aromatic and aliphatic aldehydes, secondary amines and terminal acetylenes under solvent-free conditions at 110 ºC for 10 min to provide propargylic amines in good yields (Scheme 9). The reaction between benzaldehyde, piperidine and phenylacetylene was used as model reaction to scaled-up to 10 mmol and to study the recyclability of this BNPs during five runs (yields in the range of 97 to 92%).…”

Solvent-free synthesis of propargylamines: an overview

“…Yi et al proposed A 3 coupling of aldehydes, alkynes and amines, catalyzed by Pd–Cu NWs for the synthesis of propargylamines. 78 The reaction, when conducted at 110 °C showed excellent result and the required product was obtained in 10 minutes ( Scheme 38 ). Benzaldehyde with electron-withdrawing group reacted better compared to electron-donating group.…”

Solvent‐free synthesis of propargylamines via A3 coupling reaction and organic pollutant degradation in aqueous condition using Cu/C catalyst

“…Moreover, they have been successfully applied in drugs such as rasagiline, a potent cardiovascular drug. [ 5 ] Because of their vital role in many applications, numerous synthetic methods for the preparation of propargylamines have been established. [ 6–9 ] However, improvements to these synthetic methods continue to be explored.…”